Methanol → HCID 46866426, compound

HRID 2039966Notes

Reaction equation

HRID 2039966 reaction equation
[Br:1][C:2]1[CH:21]=[CH:20][CH:19]=[CH:18][C:3]=1[C:4]([NH:6][C:7]1[CH:8]=[C:9]2[CH:15]=[C:14]([CH2:16]Br)[NH:13][C:10]2=[N:11][CH:12]=1)=[O:5].[CH3:22][OH:23]>C(OCC)(=O)C>[Br:1][C:2]1[CH:21]=[CH:20][CH:19]=[CH:18][C:3]=1[C:4]([NH:6][C:7]1[CH:8]=[C:9]2[CH:15]=[C:14]([CH2:16][O:23][CH3:22])[NH:13][C:10]2=[N:11][CH:12]=1)=[O:5]

Participants

4

Reactant 2

HCID 887MethanolHCID 86660456HCID 86660456, compound

Product 1

HCID 46866426HCID 46866426, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A flask is charged with 200 mg (0.49 mmol) of 2-bromo-N-(2-(bromomethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)benzamide (stage 1) and 5 mL of methanol. The solution is stirred at room temperature for 18 hours and then diluted in 100 mL of ethyl acetate, washed with 3×30 mL of water, dried over sodium sulphate and evaporated under reduced pressure. The raw product is then purified by silica gel chromatography (ethyl acetate/petroleum ether eluent). 30 mg of a yellow solid is obtained (17%).

Workup

  1. washwashed with 3×30 mL of water
  2. dry with materialdried over sodium sulphate
  3. customevaporated under reduced pressure
  4. customThe raw product is then purified by silica gel chromatography (ethyl acetate/petroleum ether eluent)

Sources & evidence

ORD record
ord-526f0331f1c0400b8dc9d4b0c89d3d51
Source dataset
uspto-grants-2013_11
Patent number
US08580815B2

Reaction notes

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